It was easy to project the risks. The Oilers were broadly seen as ripe for offer sheet in a bull market with first substantive revenue bump post covid. Jackson was hired in large part for his experience as a super agent fluent with the CBA and all the nuances. He was also experienced with client relationships and the issues with Broberg and agent went back virtually to his start with the organization. Deteriorated into a public trade request complete with confusion whether or not the agent had been granted permission to seek a trade. The trade request never rescinded.
Further salt in the wound your noted 'greaseball' agent (doing his job throughout the player organization development disconnect) worked with Jackson in the same agency. In fact, the two of them worked on McDavid's exceptional status petition together. There should have been no surprises in terms of situation, status player organization relationship, nor the motivations of the agent involved - already expressed to the team and a known professional work associate to Jackson.
You make it sound like the guy running a billion dollar business, trained as a lawyer and experienced as a super agent and with prior team experience were innocent babes in the woods falling victim to conditions they either blatantly ignored or were woefully naive. Further reported that a similar ignored Holloway agent with one lone client felt stonewalled himself with the Oilers organization so reached out to Ferris for advise and voila the double jeopardy trap established through inaction by the former super agent and management team.
The Oilers didn't get knifed by anyone. This was self inflicted wounds in which they ignored all the risk factors, went on a July 1 spending spree including players like Josh Brown and Stetcher while not prioritizing any action with their two pedigree blue chip players fresh off strong support in a game 7 Cup Run. Inaction unfortunate had consequences and the market reset the value on two low hanging quality young talents on a team that blew past its imposed allowance on July 1 and felt there was no need to actively negotiate or explore contingencies ... with a natural starting point with St. Louis with whom there was multiple reports of ongoing trade deadline discussion for both players mere months before. It should have mattered what the Oilers offered because had they done any simple pro-active negotiation with one or both players they quite possibly had avoided double jeopardy and kept their options open instead of passively letting the market squeeze them having placed themselves into cap purgatory.
It's an embarrassing, historic misstep. One that was widely reported as a threat within new market conditions, a damaged player reputation, and professional working relationship with the agent involved. Lots of talk about improving development from Jackson on day 1 hiring yet when it came to this team's NHL playoff steeled young future, there was no pro-active effort to talk about the plans for them nor any negotiation with the Cup run they all rode on together.